Beautiful, spacious waterfront home, an easy walk to historic Chestertown

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A spacious kitchen with wooden cabinets, a large island, and a dining area with a sofa and table.
A spacious dining area with a wooden table and chairs, a chandelier, and a view into the kitchen.
A deck with wicker furniture and a grill, overlooking a lake with a dock and trees.
A wooden pier leading to a brick building with a balcony, surrounded by trees and a sandy beach.
A spacious kitchen with wooden cabinets, a central island with stools, and a large window providing natural light.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Family fun awaits
    Top-rated for families.
  • Beach equipment
    A rare find — beach equipment ready to go for your days by the sea.
  • Discover nearby landmarks
    Near Washington College

Popular amenities

  • Balcony
  • Arcade/game room
  • Barbecue grill
  • Garage parking available
  • Air-conditioning
  • Refrigerator

Explore the area

View in a map
Chestertown, MD
  • Place, Washington College
    ‪8 min walk‬
  • Place, River Arts Chestertown
    ‪8 min walk‬
  • Place, Chestertown Historic District
    ‪9 min walk‬
  • Airport, Baltimore, MD (MTN-Martin State)
    ‪126 min drive‬

Rooms & beds

6 bedrooms (sleeps 14)

Duck Bedroom

1 Queen Bed

Green Bedroom

1 Queen Bed

Library Bedroom

1 Queen Bed

Map Bedroom

2 Single Beds

Master Bedroom Suite

1 King Bed

White Bedroom

+1
4 Single Beds and 1 Queen Bed

5 bathrooms, 2 half bathrooms

Green Bathroom

Bathtub or shower · Toilet

Ground floor bathroom

Bathtub or shower · Toilet

Jack-n-Jill

Bathtub or shower · Toilet

Main Hall Bathroom

Toilet

Map Bathroom

Bathtub or shower · Toilet

Master Bathroom

Toilet · Shower only · Jetted bathtub

Side Hall Bathroom

Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Garden

Add dates for prices

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About the area

Chestertown

Located in Chestertown, this holiday home is in the city centre and on the waterfront. Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater are cultural highlights, and some of the area's attractions include Schooner Sultana and Larrabee Arts Center. Crumpton Auction and The Mainstay are also worth visiting. Kayaking, power boating and fishing offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby.
View more Holiday homes in ChestertownOpens in a new window
Map
Chestertown, MD

What's nearby

  • Washington College - 8 min walk - 0.7 km
  • Historical Society of Kent County Maryland - 8 min walk - 0.7 km
  • River Arts Chestertown - 8 min walk - 0.7 km
  • Chestertown Historic District - 9 min walk - 0.8 km
  • Sumner Hall - 12 min walk - 1.1 km

Getting around

  • Baltimore, MD (MTN-Martin State) - 104 min drive

Restaurants

  • ‪Royal Farms - ‬3 min drive
  • ‪McDonald's - ‬3 min drive
  • ‪Dunkin - ‬3 min drive
  • ‪Procolino's - ‬3 min drive
  • ‪Royal Farms - ‬5 min walk

Frequently asked questions

Is Beautiful, spacious waterfront home, an easy walk to historic Chestertown pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Beautiful, spacious waterfront home, an easy walk to historic Chestertown?

As of 30 Oct 2026, prices found for a 1-night stay for 2 adults at Beautiful, spacious waterfront home, an easy walk to historic Chestertown on 18 Jan 2027 start from £3,951, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Beautiful, spacious waterfront home, an easy walk to historic Chestertown?

Limited spots are available.

What time is check-in at Beautiful, spacious waterfront home, an easy walk to historic Chestertown?

Check-in begins at 4:00 PM.

What time is check-out at Beautiful, spacious waterfront home, an easy walk to historic Chestertown?

Checkout is at 10:00 AM.

Where is Beautiful, spacious waterfront home, an easy walk to historic Chestertown located?

Located in the heart of Chestertown, this holiday home is within a 10-minute walk of Historical Society of Kent County Maryland, Chestertown Historic District and Garfield Center for the Arts at the Prince Theater. Chestertown Farmers Market and Washington College are also within 10 minutes.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 21 out of 26 reviews
Rating 8 - Good. 5 out of 26 reviews
Rating 6 - Okay. 0 out of 26 reviews
Rating 4 - Poor. 0 out of 26 reviews
Rating 2 - Terrible. 0 out of 26 reviews

9.6/10

Cleanliness

10/10

Check-in

9.4/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

8/10 Good

Liked: Cleanliness, check-in, location, listing accuracy
Disliked: Communication

Family Vacation

We had a great time
Stayed 5 nights in Aug 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property is in a great location and beautiful setting. We had group from college celebrating a commitment party of our college friends
Stayed 5 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great House

The whole family enjoyed this beautiful house. We also enjoyed the convenience of the dock right outside the backyard. The short walk into town was also nice
Stayed 4 nights in Jul 2023
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
The home is extremely spacious for a large group/family in town for a visit. The property is situated on a gorgeous lot overlooking the river; providing various water activities and an expansive dock to enjoy. The host/house manager was lovely, quick to communicate and accommodating for our group, something we were very appreciative of. The home is situated within a short walking distance to the center of town which was delightful! Our only suggestion would be to monitor the cleaning crew after guest check-out. We were certainly provided with fresh linens, towels and basic supplies & the home was certainly vacuumed/lightly dusted; however for the total cost of our rental, we were disappointed to see cobwebs (with spiders) in the guest rooms/throughout the home, dust bunnies and some much needed updates to carpeting/certain guest beds, that would only benefit the home substantially; however it is extremely spacious and livable space for a large group to enjoy. We appreciated the basic kitchen supplies as well as the outdoor kayaks/water activities upon a number of other activities they provide for your stay. Truly a special home and location!! Would certainly recommend!!
Stayed 3 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome stay on the Chester River

Perfect spot for our whole family to be together. It has it all. Everything worked. Super comfy. Thank you!!!!
Stayed 5 nights in Sep 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family reunion

The house was perfect for a multi-generational family reunion. The house was clean, and the kitchen, bedrooms and bathrooms had everything we needed for our stay. The property manager was very helpful and easy to contact with questions. We enjoyed the water and beach and walking to Chestertown.
Stayed 21 nights in Jul 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Looking for the perfect getaway? This is it!

The property was ideal for a family vacation. Despite the hot weather outside the property inside provided comfortable and spacious surroundings with a magnificent view of the river. It is close to the center of the town of Chesterfield with many shops, restaurants, and historical buildings within s short walking distance. The people of the town are most engaging-helping to make the stay memorable. A very special home in a very special place.
Stayed 7 nights in Jul 2024
Verified review

8/10 Good

Liked: Check-in, location, listing accuracy
Disliked: Communication

Bridgeway Community Church

This is the second year we stayed there. We met with the agent to explain what we rented the home for. She agreed and we rented the property. This year, although she had my direct cell number, she left me a note on the island about everything she was disappointed in from the previous year—everything we discussed in person before renting the home. In addition, the first year, I spoke with her and shared some things that needed to be fixed in the home, and when we returned this year, none of the items but the ice maker were fixed.
Stayed 6 nights in Aug 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay on the water for family and friends!

This property is huge and has everything you need to enjoy a waterfront vacation. We stayed with a group that was in town for a wedding. A beautiful quiet neighborhood within walking distance to everything in charming Chestertown. It was also great to have access to the kayaks and get on the water! The house was very clean but could benefit from some repairs. The deck needs to be redone and wasn’t as nice as the rest of the house. Especially the deck railing which was unstable, so we kept the kids away from it. Quite a few windows were inoperable due to the visible foundation issues. Additional seating on the deck and in the yard, extra pillows and blankets would have been nice, but overall would recommend this lovely waterfront home!
Stayed 4 nights in May 2023
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
A beautiful house in a fabulous location. We were within walking distance to town and the waterfront could not be beat. If you have a boat or are renting a boat, the home's dock provides excellent access. The Chester River water is warm for little swimmers and the provided paddle boards were a bonus.There was a heat wave when we arrived and we had issues with the air conditioning, but the owner had a serviceman out the next morning and all was resolved.The home easily accommodates a large family - we had our five children with us and two grandbabies. There was plenty of space for sleeping, eating and family games.
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was our third time staying here and we'll probably be back. It's a great house in a great location. A tree branch fell down across the lower driveway entrance one evening and the owner was very fast to respond and get it removed. As for very minor complaints: the ice machine wasn't working and the only frying pan is warped, so it doesn't work well on the induction cook top (nothing we couldn't work around).
Stayed 7 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent House!

The house was everything we could have hoped for. Great location, plenty of space, clean, and spectacular views. We've already booked it for next year!
Stayed 6 nights in Aug 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house for a relaxing family and friends get-together

Rental process was very easy
Stayed 4 nights in Jul 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relax at River in Chestertown

My family and I enjoyed our stay in Chestertown. It was 11 of us… 9 adults and 2 teenagers (13 &15). The house with all the gorgeous views were so relaxing and peaceful. The house was spotless. We did early morning walks throughout the town and stopped at Evergrain bakery for bread and cinnamon rolls. Some days we rode the bicycles and that was fun. Everything was easy to find and the property manager was very helpful. Lovely house, lovely town, lovely people and a lovely stay!
Stayed 7 nights in Jul 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place for a family gathering!

We’ll appointed and equipped house for a real Chester River experience. Access to the River and walkable to Chestertown makes this a special place to stay.
Stayed 4 nights in Jun 2022
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Wedding Weekend

We enjoyed the property very much. It is a spacious home with beautiful views and great backyard. It is an easy walk to the downtown in a very pretty neighborhood. The house fits many people and all the rooms are big and very comfortable. It was a fun time with my family!
Stayed 3 nights in Oct 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Weekend

Fantastic spot for a great weekend!!!
Stayed 3 nights in Sep 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Stay in Chestertown

We were a group of 3 families with kids ranging in age from 3 to 8. We had such a wonderful time at the River Retreat. The space is great for a large group, the "bunk room" perfect for kids who want to bunk together, and the river views, kayaks, and short walk to town make it perfect. Thank you!
Stayed 2 nights in Sep 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful house and property

It is a very spacious beautiful house. Many indoor and outdoor toys to keep us entertained. Great responses when we needed to communicate. Lovely neighborhood and within walking to town. Only disappointment was how shallow the water at the dock was during low tide. We ended up renting a slip at the Chestertown marina which was close by so our boat trips were not limited by the tide.
Stayed 7 nights in Aug 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Fun

Thanks so much for a wonderful home base for our extended family vacation. The house was perfect for us - clean, spacious, great location and management was easy to work with. We will be back!
Stayed 7 nights in Jul 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Chestertown

My family and I thoroughly enjoyed our stay in Chestertown. The house is amazing and the views were breathtaking. It was nice to have the dock where we could keep our boat. We look forward to coming again in the future.
Stayed 6 nights in Jul 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Chestertown's Best

The home was impressive with a lot of room for our multiple families to stay. Large kitchen, dinning and bedroom areas. We enjoyed the ability to take the Kayaks out on the water, walking downtown for ice cream and bake goods. We enjoy Chestertown with this being our second stay in the area. We will be back I am sure.
Stayed 7 nights in Jul 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

It was great, we had family members from age 3 to 83 and everyone enjoyed themselves.

So convenient would def recommend it.
Stayed 5 nights in Jun 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing Home

This home exceeded our expectations in every way. The property was exceptionally clean and well maintained. We enjoyed the water views and kayaks and exploring the nearby town on foot and on bikes. We rented the home for a special celebration and we are very happy with our stay.
Stayed 4 nights in Jun 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great long weekend stay!

Very cool house with all the amenities we needed for a great long weekend stay. Loved the view in the morning with coffee and house had so many areas to relax in. Screened porch in basement was really nice and loved the billiard room. It was also really cool that it is just a short walk to lots of shops and restaurants. There were several unexpected surprises like a firepit and commercial ice maker that were nice to have. Would definitely stay here again in the future.
Stayed 3 nights in Jun 2021
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